tert-Butanol → HCID 23070937, compound

HRID 501410Notes

Reaction equation

HRID 501410 reaction equation
C([N:4]([CH:7](C)C)CC)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.[C:27]([OH:31])([CH3:30])([CH3:29])[CH3:28].C([CH:35]1[CH2:40][CH2:39][CH2:38][N:37]([C:41]([O:43][CH2:44][CH:45]2[C:57]3[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=3[C:51]3[C:46]2=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:42])[CH2:36]1)(O)=O>C(OCC)(=O)C>[C:27]([O:31][C:7]([NH:4][CH:35]1[CH2:40][CH2:39][CH2:38][N:37]([C:41]([O:43][CH2:44][CH:45]2[C:57]3[CH:52]=[CH:53][CH:54]=[CH:55][C:56]=3[C:47]3[C:46]2=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:42])[CH2:36]1)=[O:17])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2756141Fmoc-3-carboxypiperidine

Product 1

HCID 23070937HCID 23070937, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

1.84 g of diisopropylethylamine and 4.71 g of diphenylphosphorylazide were added to 10 ml of a t-butanol solution of 5.01 g of 9H-fluoren-9-ylmethyl 3-carboxypiperidine-1-carboxylate, and the mixture was heated at 60° C. under a nitrogen atmosphere for 18 hours. The reaction solution was cooled, and 150 ml of ethyl acetate was added thereto. The organic layer was washed successively with 100 ml of 5% aqueous sulfuric acid, 100 ml of 5% aqueous sodium bicarbonate solution, 100 ml of water, and 100 ml of a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 1.88 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (4:1).

Workup

  1. temperatureThe reaction solution was cooled
  2. washThe organic layer was washed successively with 100 ml of 5% aqueous sulfuric acid, 100 ml of 5% aqueous sodium bicarbonate solution, 100 ml of water, and 100 ml of a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ad8e6360506424e81355a2eeb32dacd
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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